History TearJerker / TheCupheadShow

* You can't help but feel sorry for the Devil at the end of "A Devil Christmas" when he trudges back to his throne miserably after spending a long and painful night of serving the role as Santa only for the latter [[YankTheDogsChain to change his end of their deal to the joy of being nice instead of a toy train behind his back]]. (And the Devil [[VillainHasAPoint ''did'' have the right to be angry at him for doing so]]). It does turn to heartwarming however when Henchman goes out of his way to build the Devil a toy train himself.

* The whole situation with Cuphead’s soul debt from Mugman’s side during seasons one and two, when you think about it. His brother’s recklessness has gotten him in trouble with the actual Devil, who is now hunting after Cuphead’s soul. Sure, the brothers have managed to evade the Devil from collecting, but they haven’t yet found a permanent solution to this problem (prior to the reveal in season 2’s finale). The fact that Cuphead is so dismissive of the issue of his life being at stake and Mugman having to save him from several close calls as a result can’t be easy on him.

* Cuphead’s nightmare in “Sweater Off Dead” showcases in no uncertain detail that for all of Cuphead’s bravado, deep down, he’s a still a scared kid with a debt to pay to the Devil who will stop at nothing to collect.
** Moreover, it’s not just himself he’s worried about. He’s ''terrified'' at the prospect of his brother and Elder Kettle getting caught in the crossfire of his mess with the soul debt.
** According to Mugman, Cuphead’s been having these nightmares for a while. How many nights has Cuphead woken up screaming from his nightmares and how many times has Mugman listened to his brother still insist he’s fine when he clearly isn’t before finally putting his foot down to do something more proactive about the situation?

** Ms. Chalice bailing on the brothers at the cookie factory when the cops show up. At first she struggles to get the brothers awake so they can get out too, but to no avail. She confesses that she likes them but not enough to tango with the police. When she turns into a ghost, she has a look of regret on her face before she flies away. If you look closely at Ms. Chalice as she tries to get the brothers up, specifically where you can see her shaking in fear before confessing, she looks just about [[BreakTheCutie close to tears]].
* [[{{Cliffhanger}} The]] [[DownerEnding ending]] of "The Devil's Pitchfork". Despite Cuphead seemingly having the upper hand against The Devil by having his pitchfork and no longer owing him his soul, The Devil proves just how conniving he is by taking ''Mugman'' in retaliation. In the end, all Cuphead can do is look on, horrified, as his beloved brother is taken away and dragged to the underworld.

*** At first, Cuphead can't even get himself to say what happened despite several attempts, and [[BlatantLies ends up half-heartedly lying and saying what he lost was his pocket knife.]]

** This culminates in a scene where Chalice is getting ready for her DanceOff with the Devil and Mugman attempts to talk her out of it. Chalice's response? She doesn't have anything to lose. ''Ouch''.

*** At first, Cuphead can't even get himself to say what happened despite several attempts, and [[BlatantLies ends up half-heartedly lying and saying what he lost was his pocket knife.]]

** At first, Cuphead can't even get himself to say what happened despite several attempts, and ends up half-heartedly lying and said what he lost was his pocket knife.
--->'''Cuphead:''' ''(tearfully)'' Don't worry, Mugsy... I'll find ''some'' way to bring you home!

** When Elder Kettle sees Cuphead's despondence, he tries to comfort him, saying, "It's not like you lost ''Mugman.''" That's all it takes for his son to start blubbering inconsolably. Creator/Tru Valentino's [[SugarWiki/HeReallyCanAct acting]] just hammers it home here.

** When Elder Kettle sees Cuphead's despondence, he tries to comfort him, saying, "It's not like you lost ''Mugman.''" That's all it takes for his son to start blubbering inconsolably. Tru Valentino's [[SugarWiki/HeReallyCanAct acting]] just hammers it home here.

** At first, Cuphead can't even get himself to say what happens despite several attempts, and ends up half-heartedly lying and said what he lost was his pocket knife.

** From Cuphead's perspective as well. Unlike in the game he didn't know that he was betting his soul. All he wanted was to play a carnival game and now he has a soul debt on his head, which, despite insisting otherwise, he's clearly very worried about.
* Cuphead’s nightmare in “Sweater Off Dead” showcases in no uncertain detail that for all Cuphead’s bravado, deep down he’s a still a scared kid with a debt to pay to the Devil who will stop at nothing to collect.

* The whole situation with Cuphead’s soul debt from Mugman’s side, when you think about it. His brother’s recklessness has gotten him in trouble with the actual Devil, who is now hunting after Cuphead’s soul. Sure, the brothers have managed to evade the Devil from collecting so far, but they still haven’t yet found a permanent solution to this problem. The fact that Cuphead is so dismissive of the issue of his life being at stake and Mugman having to save him from several close calls as a result can’t be easy on him.

* [[{{Cliffhanger}} The]] [[DownerEnding ending]] of "The Devil's Pitchfork". Despite Cuphead seemingly having the upper hand against The Devil by having his pitchfork and no longer owing him his soul, The Devil proves just how conniving he is by taking ''Mugman'' in retaliation. In the end all Cuphead can do is look on, horrified, as his beloved brother is taken away and dragged to the underworld.

** Prior to this twist, the episode did a good job almost making you pity the Devil and how low his reputation had sunk. He was mocked in the paper for losing all his VillainCred because of Cuphead, and in his attempts to show he still has it, loses his pitchfork and is humiliated relentlessly with it by his enemy. After he accidentally blabs that he can't even take Cuphead's soul anymore, and thus is powerless to stop him anyway, he breaks down sobbing, at which point Cuphead seemingly shows sympathy......only to YankTheDogsChain and zap him again, laughing at his misery. No wonder the guy snapped.
* The teaser for season 3 which picks up right where season 2 left off, with Cuphead being absolutely ''[[HeroicBSoD devastated]]'', [[HeroicBSoD saying Mugman's name over and over again all the way home processing what just happened.]]

* The misunderstanding in “Dirt Nap” from Elder Kettle’s perspective. Imagine overhearing that the two boys you've raised with love and have always cared for think that you're old and disgusting, and want to kill you and bury you in the backyard to "put you out of your misery." His tearful confession to them of this belief near the end of the episode is heartbreaking. Even with the PoorCommunicationKills aspect some of the scenes can be really sad. Especially when Elder Kettle looks at himself in a pot and says "maybe ''I AM'' disgusting..."

** Ms. Chalice bailing on the brothers at the cookie factory when the cops show up. At first she struggles to get the brothers awake so they can get out too, but to no avail. She confesses that she likes them but not enough to tango with the police. When she turns into a ghost, she has a look of regret on her face before she flies away. If you look closely at Ms. Chalice as she tries to get the brothers up, and you see her shaking in fear before confessing, her face looks like [[BreakTheCutie she's close to tears]].

** It gets worse when you remember that his nightmare from "Sweater Off Dead" involves Mugman being taken away from him. This is his worst nightmare, come to life.

* The teaser for season 3 which picks up right where season 2 left off. Cuphead is absolutely [[HeroicBSoD devastated. He's just saying Mugman's name over and over again all the way home processing what just happened.]]